Biggest ‘What-If’ questions in Portland Trail Blazers history

What if?

It’s no secret that the Portland Trail Blazers have been through some rough situations throughout the years. Some have been out of their control, and some have been self-inflicted; but they’ve all made fans wonder what could have been if things had gone differently.

ESPN recently aired their documentary “Going Big” about the Trail Blazers drafting center Sam Bowie ahead of Michael Jordan. The Blazers have had the first pick in the draft four times, and each time they’ve drafted a center.

The Los Angeles Lakers beat the Blazers in Game 7 of the 2000 Western Conference Finals. (Photo: Robert Hanashiro/USA Today)

What if Portland Won the 2000 Western Conference Finals?

The Trail Blazers had one of the most talented teams in the NBA for the 1999-00 playoffs. They made it to the Western Conference Finals against the Los Angeles Lakers, and they had a double-digit lead heading into the final period of game seven.

But then the collapse of all collapses took place, and the team fell short of making a championship appearance.

That loss was the beginning of the end for the “Jail Blazers” of our time. Seeing the team start over with good character players was refreshing for fans in the area, but with a number of losing years ahead, it would have been interesting to see how long that team could have found success had they won a championship that season.

What if Brandon Roy Stayed Healthy?

The Blazers looked like geniuses when they traded the draft rights to Randy Foye for the draft rights to Brandon Roy. The former Washington Husky hit the ground running winning Rookie of the Year, making three All-Star appearances and becoming arguably a top-3 shooting guard in his first four seasons.

Roy hit his prime early, but that was a blessing for the Blazers, as he was forced to retire with two bad knees.

If Roy had stayed healthy, there’s no saying what his potential would have been. By the time Kobe Bryant retired, Roy could have been the best at his position, and he could have been the No. 1 scorer on a growing team out West for years to come.

What if Bill Walton Stayed Healthy?

The Blazers made their first playoff appearance in 1977, and they went all the way to the NBA Finals and defeated the Philadelphia 76ers. They had a great team that year, and the center piece was big man Bill Walton.

But like so many of Portland’s potential greats, Walton’s health hindered how far he would go with the team. An entire season missed to injuries led to his departure from the organization, and it ultimately led to the dismantling of a potential dynasty early in the team’s days as a franchise.

What if Portland Drafted Kevin Durant?

The 2007 draft had some serious hype surrounding it. We all knew that Greg Oden and Kevin Durant were going to be No. 1 and No.2 selected, but the question was, would the Blazers go with the most talented player in college basketball or a once-in-a-lifetime center?

We all know who they chose, and we all know how it’s worked out.

The Trail Blazers could have had these two guys on the same team. (Photo: Getty Images)

Oden has played in just 82 games since being drafted, and he now finds himself out of the league—at least for now. Durant on the other hand is considered a top 2 or 3 player in most NBA circles, and he is the kind of player who can single-handedly turn around a franchise.

Alternate Question: What if Oden Stayed Healthy?

Durant is a world-class basketball player, but you can’t forget that Portland chose Oden for a reason. If he had stayed healthy, he had the potential to be one of the best centers in the game at this point in his career.

What if Portland Drafted Michael Jordan?

The Blazers entered the 1984 draft with the second pick, and the one thing that they knew is that they needed a center. With Hakeem Olajuwon off the board to the Houston Rockets, Portland looked right past Michael Jordan and straight to Kentucky Wildcats big man Sam Bowie.

As we now know, Bowie never lived up to expectations, and Jordan went on to become arguably the greatest of all time.

Alternate Question: What if Portland Won the Coin Toss?

The Rockets earned the first pick because they won a coin toss before the draft. If the Blazers had won the coin toss, they would have paired Clyde Drexler with Olajuwon.

Those two went on to win two championships toward the end of their playing days, but if they had spent their entire careers together, they could have done some serious damage in Trail Blazers uniforms.